The Villainous Harlequin is the product of the popular view of The Jester, which is that of an idiotic buffoon. (This is despite the fact that The Jester was one of the most insightful members of a king's court, due to his position outside the usual social ranks.) Interestingly, in some Renaissance art Death itself is often portrayed dressed in motley, or "pied" clothing, which is often conflated with the true Harlequin outfit. The more danger a Villainous Harlequin poses to the protagonists, the closer he or she gets to Monster Clown.

The Juggler in Bt X. Dressed like a harlequin/jester, with a funny mask and a B't named 'Vanilla Fudge', you wouldn't expect this character to be one of the most fearsome, powerful and outright sadistic of the Demon Generals that guard the Area.

The Joker has wobbled between More Monster / More Clown depending on the decade, with the 50s and 60s leaning most strongly to the latter. Interestingly, the addition of his sidekick Harley Quinn (who takes this to a literal example) ends up balancing the 'more Monster' situations. It's interesting to note that Harley is only Played for Laughs when she's fawning over The Joker. When she goes out on her own, especially when she's out to prove herself to The Joker, she takes a serious level in bad ass and becomes a dangerous threat to even Batman himself.

The Joker's one-time sidekick Gaggy (a dwarf in a jester costume) also fits. The character was recently revived in Gotham City Sirens where he sought vengeance on Harley Quinn whom he viewed as having taken his place.

The Charlton/DC villains Punch and Jewelee are a married couple who both fit this role, as did the version of Toyman who was a member of the Legion of Doom on the Superfriends.

And Molly was just one of four DC villainesses to use the name The Harlequin over the years, not including Harley Quinn (who doesn't count because she spells it different...and it's a shortened version of her real name).

Pierrot Lunaire is a foe of the Musketeer who dresses as the Commedia dell'Arte character Pierrot. He was a member of the Club of Villains that appeared in the Batman R.I.P. storyline.

Averted in Astro City — Jack-in-the-Box may have the Joker's fashion sense, but he's definitely a hero.

Many, many villains from Power Rangers. Rita Repulsa (even when she was the Big Bad), Jindrax (from Wild Force) and Marah/Kapri (from Ninja Storm) are probably the most straight examples of this trope.

One episode of The Fresh Prince of Bel-Air has Will, Carlton and Uncle Phil dealing with one of these, who demands to be taken to the courthouse (where Phil is to preside over a trial that will be televised) just so he can show his act in front of the cameras. He uses dynamite sticks strapped to his body in order to persuade people into following through with him. However, the bombs later prove to be gag props complete with a "BANG!" flag. He's promptly kicked out of the court for his troubles.

In the Dungeons & Dragons 3.5 Edition Monster Manual IV is a creature called the Taunting Haunt, the vengeful spirit of a clown or preformer that can only be destroyed if beaten in a game of wits.

Champions has the Black Harlequin, a cheerful, smiley villain who just wants to have fun. His signature wepaons are armies of lethal toys, like teddy bears with metal claws, toy soldiers with real rifles and a rag-doll that causes aneurysms.

Overlord has the Minion Jesters, whose duties are to give their Evil Overlord Masters amusing names (or make little limericks in the sequel) while also serving as their Training Dummies at times.

Played with in regards of the Royal Jester in Princess Maker 2. Everyone thinks he's a bad guy and going talk to him actually drops your daughter's social reputation each time, but he's actually a rather good-hearted fellow... if a bit of a Trickster Mentor to the heroine. Who can choose being a Jester as her main work in the end, if some requirements are met (specifically, having him give her his Royal Harp after several visits, as well as possessing a strong Constitution and very high Art and Conversation skills).

The Dark Wings from Tales of the Abyss subvert this troupe. Initially they seem to be a trio of annoying (if relatively harmless) thieves disguised as circus clowns, but they're actually in league with Asch, putting them at least slightly on the side of good.

The Riddler's Gammon comics by MS Paint Adventures' Andrew Hussie feature a harlequin who menaces people with nonsensical puzzles and complicated rhyming schemes. He tends to get arrested, or shoved into garbage.

In Homestuck every enemy gets decorated in harlequin garb near the beginning of the story.

In the KITTEN II storyline of Sluggy Freelance, the commander of a paramilitary group devoted to battling the forces of evil is inexplicably dressed as a clown, which terrifies the normally-stoic Riff. It turns out he isn't really a clown, it's just a disguise to divert attention away from them. Somehow. But then it turns out that he's gone insane and believes himself to be chosen by God to control The Evil. And then it turns out that he was a clown all along.

Though being Axe Crazy with main motivation It Amused Me and appearance heavily inspired by traditional Harlequin costume, she's usually played as Humanoid Abomination rather than this with Harlequin part further highlighting her otherness.

In a Squidbillies episode, Rusty and Early become Clowny Freaks (a parody of Juggalos). To advance up the Ziggurat of the Clownies towards full ninjahood, aspiring clowny freaks must smash stuff while playing "that evil-ass calliope". Clowny Daggers, baby!

The Jester in the "Court Musician" segment in Garfield: His 9 Lives. He keeps taunting "Freddie," the titular court musician, that if he doesn't please the king with his concerto, he faces the guillotine.

An actual royal court jester was a villain in one Woody Woodpecker cartoon; he wasn't really evil, but he was a pretty bad jester, and when the king threatened to fire him after thinking Woody was much funnier, the guy went after Woody in an attempt to keep his job. (The cartoon ended with Woody getting the job with the guy being punished by being part of Woody's act - getting pies thrown in his face.)

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